The Discerning Gent’s Guide To Cuba

There are very few places in the world that offers such a multitude of experiences to the senses as much as Cuba. Elysium Magazine thought it was about time the discerning gent donned his Panama hat ventured to the land that should feature highly on everyone’s holiday to-do list. It’s a country that needs to be visited at least once, but preferable more often, by the discerning gent looking for a holiday that will rest soul, feed the mind and guarantee an unforgettable adventure.


Cuba benefits from the tantalising tropical currents of the Caribbean that caresses the island. Steeped with the dynamic mix of music, deep history and revolutionary tales – sometimes it seems that the 105th largest country in the world is in a permanent time lock that is doing all that it can not to move with the times and forget its traditions. It’s this desire to be different that gives this island its fantastic character, and gives the discerning tourist plenty to explore.


The best time to visit Cuba is during December through to early May – this is when you’ll enjoy a constant heat in the high 20’s/early 30’s with little or no rainfall. Travelling at this time also avoids the hard rains of hurricane season (late May to November) and the discomfort of the scorching summer months. The approx 10-hour flights are available from numerous airports around the UK. Now you know when to go, it’s time to look at where the discerning gent and his good lady should go.



With most flights into the capital of Cuba, Havana is likely to be your first port of call in this intriguing country. It’s a vibrant city that’s full of sights, sounds and tastes that are best enjoyed on foot out on the streets.


The discerning gent will immediately notice is the architecture of this great city. Art Deco, colonial baroque, neoclassicism and almost Gaudí-esque experimentation as you walk through Havana’s matrix of walkways, plazas and piazzas. You’ll soon come to see the stark contrast between the grand seductive architecture and the dilapidated decay caused by years of economic fallout and abandonment.


Habana Vieja (locals call it Habana) is perhaps the best when classical architecture is on the mind. With a number of renowned main squares – Plaza de Armas, Plaza Vieja, Plaza de San Francisco de Asís and Plaza de la Catedral – you can witness hundreds of buildings with historical importance. Locals are friendly and hustlers, while numerous in number, aren’t the hard-sell that tourists might be used to from other cultures and can be dismissed with a firm and confident “no thank you”.


The influence of Che Guevara, Fidel Castro and José Martí et all is everywhere. From national museums and monuments, Revolution Square and street art on every corner – these revered men have helped shaped the DNA of the country and given millions of people hope. It’s worth delving into the history books to find out more if your interests are around the historic political shaping of Cuba. The story is immense.



Next you’ll want to get into the seat of one the most iconic sights in Cuba – classic Cadillacs, Chevrolets or Buicks all in buffed up in super-shine gloss. Hail yourselves one as a taxi for an hour or so (approx 20 Cuban Convertible Dollars) and cruise through the streets of Cuba. One road not to miss is the iconic Malecón – an 8km long sea drive that is quintessentially Cuba. Have the top down, get the shades on, sit back and enjoy!


Entertainment is well-served in Cuba. If drinking is you’re thing then a visit to El Floridita is a must. A place where they make the famous daiquiri cocktail in the hundreds each day – this place was made famous by Ernest Hemingway and his fondness for the drink. Always lively, this place guaranteed to entertain, although it is a bit of a tourist trap too.


The vibrancy of Havana is infectious. Once the sun sets for the evening its time for the live music to spill out onto the streets and you’ll soon find yourself shaking it with the locals to the salsa beat. So take the hand of your good lady, take the lead and join in.



For those after entertainment on a professional level the cabaret clubs are the place to go. The biggest is the open-air Club Tropicana made famous as a mobster favourite in the 50’s and 60’s. Now it’s a haven for those after a crescendo of bright lights, flamboyant costumes and booming voices. Sit back and enjoy as the Cubanos show you how it’s done.



If the hustle of Havana gets too much, then you’ll need to head to a place where the pace of life is slow and easy. This place is Varadero – a 20km peninsula of ivory-white sandy beaches and 5-star accommodation. The turquoise-blue sea is swept along by gentle tropical breezes from the Atlantic and there is nothing better than to be enjoying a pina colada cocktail with the sun’s rays blazing down upon you as the tide tickles your feet.


Beach life is the primary and secondary attraction of Varadero, there isn’t much else to it. But for the discerning gent and his good lady looking for some rest and relaxation this poses the best option to get some real downtime. For those looking to take the pace of the action up a notch or two, various hi-octane water sports are available from the plethora of hotels on the strip, or just keep the vibe easy with a gentle paddle on the sea with a kayak.


Seafood lovers will be in for a treat in Varadero. Fresh lobster, shrimp, and fish are a staple option on nearly every menu. Those in the mood for a BBQ will find hog roasts and steaks charred to perfection, and in sizable portions too. Succulent fruit is another blessing of this tropical island with fresh mangoes, guava, papaya and pineapple ready to delight the palate.


Although not known for its nightlife, being a Cuban city Varadero still has plenty of live music options and salsa dancing to enjoy. The discerning gent is recommended to check out Casa de la Musica or Club Mambo for a night time fiesta.



Far south of Varadero is where you’ll find Trinidad – a perfectly preserved Spanish colonial town where time stopped ticking back in the 1800’s. The cobbled streets and picturesque pastel hues of the houses make this a very worthwhile visit if you have the time to get there.


Situated on the Caribbean side of the island, its influence is not hard to miss. Here is where the pace of life really slows down to a meandering pace. It was claimed a World Heritage site back in the late 80’s which has caught the eye of the tourist. Plaza Mayor is the town’s tranquil main square which is flanked on all sides by buildings of impressive architecture.


The Museo Histórico Municipal is the place to visit to get a taste for the town’s rich history. Housed in a grand mansion, there are plenty of trinkets to browse and the skyline view of Trinidad from the rooftop really highlights the setting of the town against the backdrop of mountains to one side and the Caribbean Sea on the other. A Kodak moment for sure.


Nightlife is a definite spectacle in Trinidad. As the sun sets you get a feeling that something is rousing itself for some serious action, almost like a beast asleep all day and is now ready to limber up. Casa de la Musica in Trinidad is again the place to be, along with Casa Ficher – expect to see alfresco salsa, singing and rumba drums all night long.


A Land With So Many Possibilities

Cuba is a very special place. There aren’t many countries in the world where Art Deco beauty is juxtaposed with urban neglect – but this all adds to the character that makes Cuba so unique. Havana has all the hustle and then some for a busy metropolis with the lights and sounds to tempt even the most shy tourist, while Varadero offers a recharge point to soak up the sun and appreciate serious downtime. Trinidad has all the colour and flair of the Caribbean wrapped in a docile time warp where the word ‘rush’ isn’t in the dictionary.


But these three spots represent only a fraction of what Cuba as a country has to offer. It’s such a large island that plenty of time is needed if you wanted to see it all. Transport links are very weak (or non-existent) so this just adds to the time you’ll need to visit the southern parts of the island. But it’s easy to see why men like Sir Winston Churchill and Ernest Hemingway fell in love with the island. When the sun is this good, the food so fresh and the vibe is a refreshing ‘chill out man’ in every scenario you start to appreciate what’s really magical about this country – the culture.


Getting there

Virgin Atlantic flies to Havana twice a week. Prices from £600 return.

Amit Chakravarty

Amit Chakravarty

Amit has a refined taste for all things luxury lifestyle, with a particular penchant for men’s style. He’s keen on the latest watches – especially classic timepieces, new drinks, luxury travel, fine dining, executive technology, new gadgets and sports for the discerning gent.